The push for me was the constant fragmentation of services I paid for and content I enjoyed disappearing (eg. Star Trek TNG and The Office on Netflix).
I finally decided to attack the problem of my degraded ZFS Pool and replace all my HDD's in my ZRAID Pool with larger ones, then migrate from TrueNAS Core to TrueNAS Scale for my NAS. I wanted to take full advantage of the Kubernetes/Docker capabilities in Scale. It was nice to finally get everything organized in containers instead of FreeBSD Jails that end up being a PITA to update the underlying OS on down the road when they bump the FreeBSD major version.
It was also an opportunity to start fresh and make sure my Plex DB was saved outside the container so that even if I migrated or spun up a new container, the DB would still be intact. From there, I wanted a better way to clean up my existing library, manage ingestion of content better, and make the process of managing everything easier. So obviously Sonarr/Radarr were the solution for me. I actually still use Jackett over Prowlarr though, as it is working just fine for me and I don't see much reason to change.
Everything comes together really nicely on mobile as well with nzb360. Combine that with Tailscale for easy/seamless access and it's been a pretty smooth sailing setup so far this past year.
I have an Xbox that is in the "ambiguous" category. It's doubly confusing because it has a similar name to the XBox Series X. It's the XBox One X. I'm guessing that is getting the boot this round as well.